Chicago
In 1881 Yerkes traveled to Fargo in the Dakota Territory in order to obtain a divorce from his wife of over twenty-two years. Later that year, he wedded the 24-year-old Mary Adelaide Moore and moved to Chicago.
He opened a stock and grain brokerage but soon became involved with the city's public transportation system. In 1886, Yerkes and his business partners used a complex financial deal to take over the North Chicago Street Railway and then proceeded to follow this with a string of further take-overs until he controlled a majority of the city's street railway systems on the north and west sides. However, he never achieved his ultimate goal—a monopoly of the city's streetcar lines: the South Side's Chicago Street Railway remained forever out of his reach. Yerkes was not averse to using bribery and blackmail to obtain his ends.
In an effort to polish a badly tarnished public image, Yerkes decided in 1892 to bankroll the world's largest telescope after being lobbied by the astronomer George Ellery Hale and University of Chicago president William Rainey Harper. He had initially intended to finance only a telescope but eventually agreed to foot the bill for an entire observatory. He contributed nearly $300,000 to the University of Chicago to establish what would become known as the Yerkes Observatory, located in Williams Bay, Wisconsin.
If Yerkes could have gotten his way, Chicago would never have had any elevated railroads. So it is no small irony that his greatest legacy to the city was The Loop—a rectangle of elevated tracks enclosing Chicago's business district.
While in Chicago, Yerkes became an avid art collector. He relied upon Sarah Tyson Hallowell (1846–1924) to advise him on his purchases. After the Chicago World's Fair in 1893, she tried to interest him in the works of Auguste Rodin, which were part of the loan exhibitor of French art. Because the subject matter was controversial, Yerkes and other collectors turned the works down. Within a short time he changed his mind and soon acquired two Rodin marbles, Orpheus and Cupid and Psyche, for his Chicago mansion, the first two of Rodin's works known to have been sold to an American collector. Yerkes art collection also boasted works by the French academic painters Jean-Leon Gerome and William Adolphe Bouguereau and members of the Barbizon School.
Yerkes, hoping to escape from a city he had grown to detest, embarked upon a campaign for longer streetcar franchises in 1895. He offered Illinois governor John Peter Altgeld an enormous bribe for his support, but Altgeld rejected the bribe and vetoed the franchise bills. Yerkes renewed the campaign in 1897, and, after a hard-fought battle, secured from the Illinois Legislature a bill granting city councils the right to approve extended franchises. The so-called franchise war then shifted to the Chicago City Council—an arena in which Yerkes ordinarily thrived. A partially reformed council under Mayor Carter Harrison, Jr., however, ultimately defeated Yerkes, with the swing votes coming from aldermen "Hinky Dink" Kenna and "Bathhouse" John Coughlin.
In 1899, Yerkes sold the majority of his Chicago transport stocks and moved to New York.
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